SYNTHESIS OF 2-DEOXY-2-FLUOROHEXOSES BY FLUORINATION OF GLYCALS IN AQUEOUS MEDIA

Article abstract of DOI:10.1016/S0008-6215(00)90191-5

1,5-Anhydro-2-deoxy-D-arabino- (D-glucal), 1,5-anhydro-2-deoxy-D-lyxo- (D-galactal), and 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (3,4,6-tri-O-acetyl-D-galactal) (3) were fluorinated in water and organic solvent-water with molecular fluorine and, for ¹⁸F-labelled compounds, with <¹⁸F>fluorine.Chemical yields of 40 and 10percent were obtained for 2-deoxy-2-fluoro-D-glucose and 2-deoxy-2-fluoro-D-mannose, respectively, and 35 and 5percent for 2-deoxy-2-fluoro-D-galactose (12) and 2-deoxy-2-fluoro-D-talose (13), respectively.In the fluorination of 3, the chemical yields of 12 and 13 were 38 and 6percent, respectively.An l.c. separationof 2-deoxy-2-fluoro-D-hexoses is described.